3-(4-hydroxy-3-methoxyphenyl)propanoic acid

• ChemBase ID: 52454
• Molecular Formular: C10H12O4
• Molecular Mass: 196.19988
• Monoisotopic Mass: 196.07355886
• SMILES: C(=O)(CCc1cc(c(cc1)O)OC)O
• Canonical SMILES: COc1cc(CCC(=O)O)ccc1O
• InChI: InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
• InChIKey: BOLQJTPHPSDZHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxy-3-methoxyphenyl)propanoic acid
• IUPAC Traditional name: homovanillinic acid
• Synonyms: HYDROFERULIC ACID; Hydroferulic acid; 3-(4-Hydroxy-3-methoxyphenyl)propionic acid; 3-(4-Hydroxy-3-methoxyphenyl)propionic acid; 4-Hydroxy-3-methoxybenzenepropanoic Acid; 4-Hydroxy-3-methoxyhydrocinnamic Acid; β-3-Methoxy-4-hydroxyphenylpropionic acid; 3-Methoxyphloretic Acid; Dihydroconiferylic Acid; Shorbic Acid; Dihydro Ferulic Acid; 氢化阿魏酸; 3-(4-羟基-3-甲氧基苯基)丙酸

Database IDs

• CAS Number: 1135-23-5
• EC Number: 214-489-5
• MDL Number: MFCD00016558
• Beilstein Number: 2110370
• PubChem SID: 24850711; 162057217
• PubChem CID: 14340

CALCULATED PROPERTIES

• Acid pKa: 3.952401
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.03907997
• LogD (pH = 7.4): -1.5926294
• Log P: 1.5943261
• Molar Refractivity: 50.4107 cm^3
• Polarizability: 19.528738 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Melting Point: 87-92°C; 87-93 °C; 90-92°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥96.0% (T); 97%; 98%
• Empirical Formula (Hill Notation): C10H12O4

DETAILS

MP Biomedicals - 05203850

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 17803

Packaging
5 g in poly bottle

Toronto Research Chemicals - D448900

A caffeine metabolite which showed high antioxidant activity. It is a very sensitive biomarker for the consumption of relatively small amount of coffee.

REFERENCES

• Buchanan, C., et al.: J. Sci. Food Agric., 71, 459 (1996)
• Andreasen, M., et al.: J. Agric. Food Chem., 49, 5679 (1996)
• Poquet, L., et al.: Drug Metab. Dispos., 36, 190 (1996)